Dated a girl for over a year while in grad school. Things were getting serious then one day I saw her run. It was the running equivalent of Elaine from Seinfeld dancing. I decided right then it wasn't going to work. Broke up with her a couple months later.

Had a girlfriend in junior high for a few weeks. I heard from a friend she bought me a valentine's day gift. I hadn't bought her a gift, nor did i even know what one buys a girl for valentine's day. Needless to say I started to panic. My junior high brain decided that the only way out of my predicament was to break up with her. Classy.